1,1,3,3,3-Pentafluoro-2-pentafluorophenylpropene oxide. Precursor for novel phosphonates and ylides

✍ Scribed by Alexander A. Kadyrov; Gerd-Volker Röschenthaler

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 142 KB
• Volume: 8
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1997)8:1<59::aid-hc9>3.0.co;2-y

✦ Synopsis

1,1,3,3,3-Pentafluoro-2-pentafluorophenylpropene oxide reacted with triethyl phosphite to give the ylide C 6 F 5 (CF 3 )C‫ס‬P(OEt) 3 . Hydrolysis yielded the phosphonate C 6 F 5 (CF 3 )CHP(O)(OEt) 2 , which was dehydrofluorinated using Et 3 N • BF 3 to form the vinyl phosphonate C 6 F 5 (CF 2 ‫)ס‬CP(O)(OEt) 2 , a compound available also directly from the starting epoxide and diethyl trimethylsilyl phosphite. The vinyl phosphonate and diethyl trimethylsilyl phosphite furnished a 2:1 mixture of (Z) and (E) bisphosphonates together with fluorotrimethylsilane. Thermolylsis of the ylide gave diethyl phosphorofluoridate and 1,1-difluoro-2-pentafluorophenyl-but-1-ene.